Tetrazomine is a biologically active natural product, which has shown potent cytotoxicity activity against P388 leukemia cells in vivo and good antimicrobial activity against both Gram-negative and Gram-positive bacteria. Therefore, this compound is an exciting lead for development as a potential chemotherapeutic agent. This proposal describes an investigation of tetrazomine through total synthesis and the exploration of structure-activity relationships through analogue generation. The proposed synthesis offers many advantages such as synthetic brevity in addition to potentially high-yielding reactions. These advantages coupled with the potential for molecular modification to probe structure-activity relationships, leads to a novel and useful route to study this very interesting molecule.